You Can’t Be Afraid To Lose It | Ask Daily Stoic

The Stoics remind you that the point of financial security is to feel secure. The point of plenty is to realize that you have enough. You can’t fear losing what you had–there was a time you didn’t have it and you survived.💡The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free explores how Stoic ideas can be applied to personal finance, wealth-building, financial mindset, and how it can help you overcome common financial obstacles and challenges👉 Get The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life📚 Book Mentioned | Dying Every Day: Seneca at the Court of Nero by James Romm at The Painted Porch | https://www.thepaintedporch.com/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:05Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic-inspired meditation, designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women, help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit DailyStoic.com.

• 0:55Ryan Holiday?

  You can't be afraid to lose it. We want to think that money will make us freer. We think it'll give us the power to say no to stuff we don't want to do, to live how we want to live, to take the risks that we want to take. But will it? How has that worked out for most people in history? This is the paradox of wealth. Once we have it, instead of becoming free, we become obsessed with wanting to preserve our money, with not wanting to lose it, with wanting more of it. When Seneca said that slavery resides beneath marble and gold, he wasn't just talking about the time and cost and upkeep of nice stuff. He was talking about how easily we become prisoners of the status quo. That's why he would often experiment with what it was like to be poor, dressing in rags, going without food.

• 1:38Ryan Holiday?

  He wanted to be able to say, is this what you feared? He wanted to remind himself that losing what he had wasn't so bad. And it's good that he practiced this because Seneca did lose much of what he had when he left Nero's service. Although whether he should have gotten it in the first place is a different moral question, which James Rahm discussed in his amazing book, Dying Every Day. One ancient historian noted that Nero had trouble poisoning his former advisor because the meager natural diet that Seneca reverted to presented so few opportunities. The Stoics remind you that the point of financial security is to feel secure. The point of plenty is to realize that you have enough. You shouldn't fear losing what you had. There was a time that you didn't have it and you survived.

• 2:20Ryan Holiday?

  And besides, no one can ever take from you what you learned in order to get it. And this idea of enough, it's a simple idea, this idea of feeling secure from your financial security, this is simple enough, but of course, it's very difficult. It requires a certain amount of self-awareness, a certain amount of discipline, requires, I think, some study and understanding and wisdom. And that's what we built The Wealthy Stoic on. The Wealthy Stoic, A Daily Stoic Guide to Being Rich, Free, and Happy, I think, is one of our best courses. It's a deep dive into what the Stoics thought about money, how to be wealthy in every sense of the word, not just to have a lot, but to feel like you have a lot, to feel like you have enough, to feel secure, to feel good, right? To feel good and secure even when you don't have much.

• 3:04Ryan Holiday?

  It's nine weeks and to deep dive into the ambitions and motivations that fueled the Stoic definition of wealth and success, how to find your own definition of wealth and success, how Stoics spent and saved money, what the Stoics prized above money, a bunch of other stuff. It's great. I think you'll love it. There's deep dives and interviews with me and some great minds on money also, including the one and only Morgan Housel, my friend Cal Newport, Ali Webb, who's a hugely successful entrepreneur, a bunch of awesome stuff. If you want to tackle your relationship with money, we'll sign up for The Wealthy Stoic, Daily Stoic Guide to Being Rich, Free, and Happy. Go through the course at your leisure. It's dailystoic.com/wealth. Or if you're thinking about signing up for Daily Stoic Life, you can do that.

• 3:46Ryan Holiday?

  Basically, for the cost of this course, you get all our courses for free, plus a bunch of awesome, really cool benefits and more stuff from me. So go to dailystoiclife.com or dailystoic.com/wealth.

• 4:02Ryan Holiday?

  Hey, it's Ryan. Welcome to a Thursday episode of the Daily Stoic Podcast. We talked about the Socratic Circle before, right? This group of Stoics that would get together in ancient Rome and talk philosophy, talk life, talk business, talk politics. And the Socratic Circle, you hear about it from Plutarch, you hear about it from Cicero. It was sort of one of the first, you could call it a mastermind group. And obviously, that's a thing now. I've belonged to a couple. I've Spoken at countless ones. I've been bringing you some excerpts of a talk I gave back in February. 10 guys from all over the country get together four times a year. They bring out a speaker. This time they all flew in Austin. I drove out to Lake Buchanan. There's like five lakes in a row going out from Austin.

• 4:48Ryan Holiday?

  And it was a very cold day. As I said, I swam in Barton Springs that morning. It was like 28 degrees and I was freezing. So you might hear some of the shivers or the chattering of my teeth in here because it took me quite a long time to get my body temperature up. But otherwise, this is me answering their questions. And if you are looking for a little Socratic circle, that's what we try to do in Daily Stoic Life. You can join us at DailyStoicLife.com. You get all our Daily Stoic courses. You get Q and As. You get a bunch of other awesome bonuses. We've been doing it a really long time. It's one of my favorite things. I get a bunch out of it and I think you will as well.

• 5:30Ryan Holiday?

  I was talking to Molly Bloom one time, you know, the Aaron Sorkin movie Molly's Game. She was the poker entrepreneur. Anyways, we were talking about someone we both knew who we always see him in pictures of private jets and whatever. And I go like, I know what their business is. The math doesn't like, I know what that costs. This isn't like private jet money. And she goes, one thing I learned that you should never forget is that that person could just be a criminal. And I was like, oh yeah, in our world, right? Most of you're like, oh, you're on the up and up. If they're beating me, it must just because they're better or smarter or got lucky or whatever. Her peek into the underbelly of a very different world. You're like, oh, they could just not be paying their taxes or they could just be, you know, this could be a fraud. The Ponzi scheme guy from the thing or whatever.

• 6:15Ryan Holiday?

  Exactly. And so I just sometimes like when I find myself being jealous, even if it's not true, I just feel like they could be a criminal. Like, you don't know. That's the justice. And then, and then I don't have to think about it, right? Then I'm all of a sudden you're not comparing yourself to that person. So that was always very helpful to me. How does AI first?

• 6:32Speaker 01

  Being a writer, an author, are you implementing anything, certain technologies in your processes? Like?

• 6:39Ryan Holiday?

  I'm thinking a lot about this, actually. The book that I'm just finishing, I tell this story at the beginning. There's this sort of wealthy Roman who, you know, he wants to be smart. He wants to impress people. And he's got money, so he could, you know, go back to school. He could learn a bunch of stuff. He could study, put in the work. Instead, he hires this group of slaves, each one who's very smart, with a specific sort of ancient writer. So he picks one who knows Homer, one who knows Euripides, one who knows Aeschylus. And then they follow him around and like at dinner parties and stuff. When he needs to say something, they whisper in his ear what he should say. And he thinks he's kind of getting away with it. You know, everyone thinks he's so smart. And a friend comes up to him and he says, you know, this is such a lovely party. You're so smart.

• 7:24Ryan Holiday?

  Have you ever thought about becoming a wrestler? Wrestling being a sort of main sport for the Greeks and the Romans. And he goes, why would I become a wrestler? I'm an old man. And then, and then his friend looks at him and goes, yeah, but your slaves are still young.

• 7:39Ryan Holiday?

  And Seneca's point is that like wisdom, like all things, it takes work and that you never get it by chance. There's no secret. There's no shortcut. There's no magical thing that just gets you what you want. I think we could say safely that our kids, their life is going to be defined by how good they are at using AI, right?

• 7:58Speaker 01

  So is my next question.

• 7:59Ryan Holiday?

  I'm thinking a lot about how do I teach them? Like it comes down to what they call prompt engineering.

• 8:04Speaker 01

  Yep.

• 8:05Ryan Holiday?

  Like, how good are you at getting what you want from this thing? Like it's a tool. It's magic, but how good are you at summoning the magic, I think is that. So I, I've been fooling around with my kids a lot. Like one of the things they did, we've done this for a year or two now, is like, if they want to color something.

• 8:21Speaker 01

  Yep.

• 8:22Ryan Holiday?

  We like work with AI to make something cool.

• 8:25Speaker 01

  For them to color.

• 8:26Ryan Holiday?

  Then we print out and they color. Or, you know, if they want to hear a story, we like ask it. Like they're putting in the inputs and then getting the outputs. Or they're like, what did that look like? And we're like, well, let's have it do it.

• 8:36Speaker 01

  Go through it, think through it, like, yeah.

• 8:38Ryan Holiday?

  So, and then going, okay, hey, the reason this isn't what you want it to be is because your question is unclear. And how do you refine it? And so kind of? Teaching them how to not just be comfortable using it, but good at using it.

• 8:54Speaker 01

  In your chat with Jay Shetty, you talked about ambition as an addiction. How do you keep your drive in check so it doesn't burn you out or blind? And you talked about it a little bit with your writing on that.

• 9:06Ryan Holiday?

  I just, I just try to be driven about stuff that I control. You know, so like if your drive is to like be the number one of this or to be recognized as that or to, you know, beat this or that, you better hope it goes the way that you want it to go. You're going to be unhappy. But if your ambition is tied, this is basically the core of Stoicism. If you're more rooted in like the parts of it you control, then no one can prevent you from getting that thing or fewer things can prevent you from getting that thing. So it's like, if my ambition is to write a really great book, it's still going to be super hard and there's no guarantee.

• 9:46Ryan Holiday?

  But I control my own destiny more than if my goal is to win the Nobel Prize for Literature.

• 9:57Ryan Holiday?

  Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything. I just wanted to say thank you.